Question

Please provide a reaction mechanism with a chair state to show how the stereochemistry was achieved. Also, please explain the reasoning/methodology behind the type reaction.

NaOEt/EtOH

Answer 1

This is an example of Robinson annelation . An annulation which means (ring-forming) condensation reaction takes place in which a ketone that contains atleast one α-hydrogen when treated with an α,β-unsaturated ketone, here in this case methyl vinyl ketone which is also called Michael acceptor. The reaction involves a Michael addition which is a 1,4 conjugate adition with the enolate followed by an aldol condensation reaction.

OEt Eto H он он Н-ОН о Н о но

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